1197214-47-3

Basic information

• Product Name: (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol
• Synonyms: (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol;(S)-5,5',6,6',7,7',8,8'-Octahydro-3,3'-bis[2,4,6-tris(1- methylethyl)phenyl]-[1,1'-binaphthalene]-2,2'-diol
• CAS NO: 1197214-47-3
• Molecular Formula: C50H66O2
• Molecular Weight: 699.05784
• Mol File: 1197214-47-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 735.8±60.0 °C(Predicted)
• Appearance: /
• Density: 1.033±0.06 g/cm3(Predicted)
• PKA: 9.27±0.20(Predicted)
• CAS DataBase Reference: (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol(1197214-47-3)
• EPA Substance Registry System: (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol(1197214-47-3)

Safety Data

• Hazardous Substances Data: 1197214-47-3(Hazardous Substances Data)

Usage

General Description

The chemical (1S)-5,5',6,6',7,7',8,8'-octahydro-3,3'-bis[2,4,6-tris(1-Methylethyl)phenyl]-[1,1'-Binaphthalene]-2,2'-diol, also known as a binaphthol, is a chiral compound with two stereocenters. It is commonly used as a chiral resolving agent and as a chiral ligand in asymmetric catalysis. The chemical structure is characterized by a central core of two naphthalene rings, with hydroxyl groups and 2,4,6-tris(1-methylethyl)phenyl attachments. Its chiral nature and structural features make it useful in the production of pharmaceuticals, agrochemicals, and fine chemicals. Additionally, it is also used in the synthesis of optically active compounds and in analytical chemistry for chiral separation.

Upstream product

• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 78229-12-6 (Ra)-3,3’-dibromo-2,2’-dimethoxy-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene 
• 21524-34-5 2,4,6-triisopropyl-1-bromobenzene 
• 791616-64-3 (R_a)-3,3’-dibromo-2,2’-bis(methoxymethoxy)-5,5’,6,6’,7,7’,8,8’-octahydro-1,1’-binaphthalene 
• 39648-74-3 (Ra)-5,6,7,8,5',6',7',8'-octahydro-[1,1']binaphthalenyl-2,2'-diol 

Relevant articles and documents

Enantioselective organocatalytic fluorination-induced Wagner-Meerwein rearrangement

Cracked under strain: Strained allylic cyclobutanols and cyclopropanols readily undergo a ring expansion described by the title rearrangement. This reaction is promoted by catalytic amounts of 1 and displays high tolerance with respect to the substrate scope. The corresponding β-fluoro spiroketone products are isolated in high yields and with excellent stereoselectivities. EDG=electron-donating group, EWG=electron-withdrawing group. Copyright

Br?nsted Acid-Catalyzed Enantioselective Cycloisomerization of Arylalkynes

The first example of an enantioselective carbocyclization of an alkyne-containing substrate catalyzed by chiral Br?nsted acids was achieved. The use of the 2-hydroxynaphthyl substituent on the alkyne as a directing group constituted the key parameter enabling both efficient regioselective protonation of the carbon–carbon triple bond and chiral induction. The key cationic intermediate could be depicted either as a cationic vinylidene ortho-quinone methide or a stabilized vinyl cation. Atropoisomeric phenanthrenes derivatives were produced in high yields and good enantioselectivities under mild, metal-free reaction conditions in the presence of chiral N-triflylphosphoramide catalysts. The carbenic nature of the cationic intermediate was also exploited to describe an example of alkyne/alkane cycloisomerization.